Abstract
By reaction of 2-vinyloxyethyl isothiocyanate with salicylic acid hydrazide a synthesis of the corresponding thiosemicarbazide was performed. Alkaline hydrolysis of the latter led to an intramolecular heterocyclization into 1,2,4-triazole derivative. When cyclization was carried out in the water-alkali medium, 2-vinyloxyethyl fragment was shown to be hydrolyzed to form 4-(2-hydroxyethyl)-5-(2-hydroxyphenyl)-2H-1,2,4-triazolo-3(4H)-thione, whose spatial structure was established by XRD analysis.
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Mashkovskii, M.D., Lekarstvennye sredstva (Pharmaceuticals), Moscow: OOO RIA Novaya Volna, 2007, pp. 163, 863.
Kolla, V.E. and Berdinskii, I.S., Famakologiya i Khimiya Proizvodnykh Gidrazina Pharmakology and Chemistry of Hydrazine Derivatives, Yoshkar-Ola, 1976, p. 263.
Gazaliev, A.M., Zhurinov, M. Zh., Nurkenov, O.A., and Kulakov, I.VX, Khimiya i farmakologiya gidrazidov (Chemistry and Pharmacology of Hydrazides), Almaty: Gylym, 2002, p. 132.
Glushkov, V.A., Mardanova, L.G., and Shavrina, T.V., Khim. Farm. Zh., 1995, no. 10, p. 12.
Mashkovskii, M.D., Lekarstvennye sredstva (Pharmaceuticals), Moscow: Novaya Volna, 2001, vol. 2, p. 306.
Mashkovskii, M.D., Lekarstva XX Veka (XX Century Drugs), Moscow: Novaya Volna, 1998, p. 320.
Dilanyan, E.R., Ovsenyan, T.R., Arsenyan, F.G., and Agoronyan, A.A., Khim. Farm. Zh., 1999, vol. 33, no. 10, p. 15.
Ibrayev, M.K., Takibayeva, A.T., Gazaliev, A.M., Nurkenov, O.A., and Fazylov, S.D., Zh. Prikl. Khim., 2006, vol. 79, no. 2, p. 328.
Ibrayev, M.K., Turdybekov, D.M., Takibayeva, A.T., Nurkenov, O.A., Turdybekov, K.M., Gazaliev, A.M., and Adekenov, S.M., Zh. Obshch. Khim., 2006, vol. 76, no. 4, p. 672.
Selezneva, E.S., Belousova, Z.P., Ivanchina, A.I., and Ten’gayev, E.I., Khim. Farm. Zh., 2006, vol. 40, no. 3, p. 27.
Ivanskii, V.I., Khimiya Geterotsyklicheskich Soedinenii (Chemistry of Heterocyclic Compounds), Moscow: Vysshaya Shkola, 1978, p. 559.
Berim, I.G., Khimicheskaya zashchita rastenii (Plant Chemical Protection), Saint-Petersburg: Nauka, 1996, p. 115.
Golyshin, N.M., Zh. Khim. Obshch. im. D.I. Mendeleeva, 1984, vol. 29, no. 1, p. 74.
Van Gestel, J., Heeres, J., Janssen, M., and Van Reet, G., Pestic. Sci., 1980, vol. 11, no. 1, p. 95.
Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc. Perkin Trans. 2, 1987, p. S1.
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Original Russian Text © A.S. Alimbayeva, O.A. Nurkenov, A.Kh. Zhakina, I.V. Kulakov, D.M. Turdybekov, K.M. Turdybekov, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 7, pp. 1175–1179.
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Alimbayeva, A.S., Nurkenov, O.A., Zhakina, A.K. et al. Synthesis and spatial structure of 4-(2-hydroxyethyl)-5-(2-hydroxyphenyl)-2H-1,2,4-triazolo-3(4H)-thione. Russ J Gen Chem 79, 1532–1536 (2009). https://doi.org/10.1134/S1070363209070226
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DOI: https://doi.org/10.1134/S1070363209070226